WO1986005358A1 - Derives de phenoxyalcenylpyridine, compositions fongicides les contenant, procedes fongicides les utilisant et procedes de preparation de ces derives - Google Patents

Derives de phenoxyalcenylpyridine, compositions fongicides les contenant, procedes fongicides les utilisant et procedes de preparation de ces derives Download PDF

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Publication number
WO1986005358A1
WO1986005358A1 PCT/US1985/000433 US8500433W WO8605358A1 WO 1986005358 A1 WO1986005358 A1 WO 1986005358A1 US 8500433 W US8500433 W US 8500433W WO 8605358 A1 WO8605358 A1 WO 8605358A1
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Prior art keywords
compound
pyridine
enyl
phenyl
lower alkyl
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PCT/US1985/000433
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English (en)
Inventor
Allan F. Rose
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Chevron Research Company
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Application filed by Chevron Research Company filed Critical Chevron Research Company
Priority to EP19850901761 priority Critical patent/EP0215778A1/fr
Priority to PCT/US1985/000433 priority patent/WO1986005358A1/fr
Publication of WO1986005358A1 publication Critical patent/WO1986005358A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • This invention relates to certain fungicidal phenoxyalkenylpyridine derivatives and to methods of pre ⁇ paring such derivatives.
  • the inven ⁇ tion relates to the application of said derivatives as fungicides.
  • U.S. Patent No. 4,262,000 describes certain 3-phenoxy-hydroxyalkanylpyridine and 3-phenoxy-ketoal- kenylpyridine derivatives as having fungicidal activity.
  • the present invention provides compounds having fungicidal activity and having especially excellent activity against bean powdery mildew pathogen and celery late blight pathogen. Moreover, certain of the compounds are active against bean rust pathogen. This is surprising since the corresponding saturated alkyl analogs and keto analogs of the present compounds, such as described in U.S. Patent No. 4,262,000, although exhibiting activity against bean powdery mildew pathogen fail to exhibit any significant eradicant activity against celery late blight pathogen nor against bean rust pathogen. The present compounds thus afford a significant and unexpected advan ⁇ tage in the treatment of these diseases.
  • Ar is phenyl, naphthyl, substituted phenyl or substituted naphthyl in each case substituted with one or two substituents independently selected from the group of halo, lower alkyl, lower alkoxy, or phenyl;
  • R is phenyl or the group having the formula:
  • R 2 is hydrogen, alkyl, having 1 through 4 carbon atoms, hydroxy, or halo
  • R 1 is hydrogen, lower alkyl, benzyl, allyl, halo- QC allyl, having 1 or 2 halo substituents independently selected from the group of fluoro, chloro, bromo and iodo, or lower alkyl carbonyl;
  • Compatible salts of the compounds of Formula I are also encompassed within the invention.
  • the compounds of the invention exist as geo ⁇ metric isomers with respect to the double bond. Moreover, the compounds also have an asymmetric carbon atom and thus can also exist as optical isomers.
  • the above Formula I is intended to represent both the respective individual geo- 25 metric and optical isomers and also mixtures thereof, and the respective individual as well as isomer mixtures are encompassed within the invention.
  • the invention also provides processes for pre ⁇ paring the above compounds.
  • the invention provides fungicidal compositions comprising a compatible carrier and an amount of the compound of Formula I effective to prevent or arrest the growth of fungi or eradicate fungi.
  • the invention provides a 5 method for controlling fungi which comprises applying an amount of the compound of Formula I, effective to prevent or arrest the growth of fungi or eradicate fungi to such fungi or to the potential growth medium of such fungi (e.g., vegetation). 0
  • the invention will be further described herein- below.
  • the preferred compounds in terms of their substituents, are those wherein Ar is 4-halophenyl, especially 4-chloro- phenyl, or 2,4-dihalophenyl, especially 2,4-dichloro- j e phenyl, or biphenyl.
  • the preferred R substituent is t- butyl.
  • the preferred R 1 substituent is hydrogen.
  • the preferred compounds are those having one or more of the above preferred substituents and most prefer ⁇ ably having a preferred substituent at each respective 20 position.
  • alkyl refers to both straight- and branched-chain alkyl groups. Generally, such alkyl groups contain from 1 through 12 carbon atoms.
  • lower alkyl refers to both straight- and branched-chain alkyl groups having from 1 through 6 30 carbon atoms and includes primary, secondary and tertiary alkyl groups.
  • Typical lower alkyls include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-hexyl, and the like.
  • halo or halogen atom
  • alkoxy refers to the group R 0- c wherein R° is alkyl.
  • lower alkoxy refers to the alkoxy groups having from 1 through 6 carbon atoms and includes,
  • lower alkyl carbonyl refers to the group having the formula
  • R 6 is lower alkyl
  • lower alkoxycarbonyl refers to the group
  • compatible salt refers to salts of the parent compound which do not significantly adversely o effect the fungicidal properties of the parent compound and are substantially non-phytotoxic at the appropriate fungicidal dosage.
  • fungicidal is a broad term and refers to either or both preventative (prevents fungicidal infec- 5 tions) and eradicant (fungalstatic - prevents the growth of fungi ultimately producing destruction of the fungus through failure to reproduce and more rarely curatic: directly causes the destruction of the fungus).
  • compatible carrier refers to sub- Q stances which can be mixed with the fungicidal compounds of the present invention which do not signi icantly adversely affect the properties of the active compound save to dilute it and are substantially non-phytotoxic. Examples of suitable compatible carriers are given in the Utility section set forth hereinbelow. Synthesis
  • the compounds of Formula I can be prepared by the following process schematically represented by the following overall reaction equation:
  • This process can be conveniently effected by contacting compound (A) with a keto reducing agent under reactive conditions, preferably in an inert organic solvent.
  • this process is conducted at tempera ⁇ tures in the range of about from -10 to 100°C, preferably about from 0 to 20°C for about from 0.5 to 5 hours, pre ⁇ ferably about from 0.5 to 1 hour using about from 1 to 4, ' preferably about from 1 to 1.5 mole equivalents of the reducing agent per mole of compound A.
  • Suitable inert organic solvents which can be used include, for example, methanol, methylene chloride, ethanol, isopropanol, tetra- hydrofuran, and the like and compatible mixtures thereof. Water and compatible mixtures of the above solvents with water can also be used.
  • Suitable reducing agents which can be used include, for example, sodium borohydride, sodium cyanoborohydride, lithium aluminum hydride, and the like.
  • ethers of Formula I wherein R is alkyl benzyl, allyl, or haloallyl can be conveniently prepared via the following schematically represented process:
  • R ⁇ is lower alkyl, benzyl, allyl, or halo ⁇ allyl and X is an anion (e.g. halide, sulfate) and n is its valence.
  • This process can be effected by contacting com ⁇ pound la with compound (E) under reactive conditions pre ⁇ ferably in an inert organic solvent.
  • this process is conducted at tempera- tures in the range of about from -20 to 100°C, preferably about from 0 to 20°C, for about from 0.5 to 12 hours, preferably about from 0.5 to 1.5 hours using about from 1 to 3, preferably about from 1 to 1.2 mole equivalents of compound R (X) ⁇ / n per mole of compound la.
  • Suitable inert organic solvents which can be used include, for example, tetrahydrofuran, dimethylformamide, toluene, and the like and compatible mixtures thereof.
  • esters of Formula I wherein R is lower alkyl carbonyl ' can be conveniently prepared via the following schematically represented process:
  • R 4 is lower alkyl and X is an anion (e.g. halide, imidazole, hydroxy, oxycarbonylalkyl, etc.) and n is its valence.
  • X is an anion (e.g. halide, imidazole, hydroxy, oxycarbonylalkyl, etc.) and n is its valence.
  • This process can be effected by contacting com- pound la with compound F under reactive conditions prefer ⁇ ably in an inert organic solvent and in the presence of a base.
  • this process is conducted at tempera ⁇ tures in the range of about from -10 to 100°C, preferably about from 0 to 40°C for about from 0.5 to 12 hours, preferably about from 0.5 to 1.5 hours using from about 1 to 3, preferably from 1 to 1.1 mole equivalents of compound F per mole of compound la and in the presence of from about 1 to 4, preferably from about 1 to 1.5 mole equivalents of base per mole of compound la.
  • Suitable bases which can be used include, for example, triethyl amine, pyridine, sodium or potassium bicarbonate, sodium or potassium hydroxide, and the like.
  • Suitable inert organic solvents which can be used include, for example, toluene, benzene, dichloromethane, chloroform, tetrahydrofuran, dioxane and the like and compatible mixtures thereof.
  • the starting materials of Formula A are gener- ally known compounds and can be prepared by known proce ⁇ dures, such as for example described in U.S. Patent No. 4,262,000.
  • the compounds of Formula A can also be prepared by the following process schematically repre ⁇ sented by the following overall reaction equations:
  • X 1 is chloro or bro o and Ar and R are as defined hereinabove.
  • the first step of this process can be effected by contacting compound C with compound D under reactive conditions preferably in water and/or an inert organic solvent and in the presence of a base.
  • This process is typically conducted at temperatures in the range of about from 0 to 150°C, preferably 60 to 100°C for about from 1 to 10 hours, preferably 1 to 4 hours using about from 1 to 2 moles, preferably 1 mole of compound D per mole of com ⁇ pound C.
  • Suitable inert organic solvents which can be used include, for example, methanol, ethanol, toluene, and the like and compatible mixtures thereof. Water can also be used as a solvent or diluent.
  • a base generates the anion of com- pound C which is a better nucleophile in the displacement of X 1 from compound D.
  • a base which can be used include sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydride, and the like.
  • the second step of this process can be effected by contacting compound B with 3-pyridinecarboxaldehyde under reactive conditions, preferably in an inert organic solvent and in ' the presence of base.
  • this reaction is conducted at temperatures in the range of about from 0 to 100°C, preferably about from 10 to 25°C for about from 1 to 48 hours, preferably 12 to 24 hours using about from 1 to 3 moles, preferably 1 to 1.5 moles of 3-pyridinecarboxaldehyde per mole of compound B.
  • Suitable inert organic solvents which can be used include, for example, methanol, ethanol, methylene chloride, toluene, and the like and compatible mixtures thereof.
  • Suitable bases which can be used include, for example, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, and the like. Typically about from 0.01 to 1.5 mole equivalents, preferably 0.01 to 0.1 equivalents, of base are used per mole of compound B.
  • the anion salts of the compounds of Formula I can be prepared by reacting the free base of Formula I with an acid having the appropriate anion or by ion exchange of one salt of Formula I with the appropriate anion exchange resin.
  • the procedures for preparing salts described in U.S. Patent No. 4,262,000, Column 12, which procedures are hereby incorporated by reference, can also be applied to prepare the salts of the present invention. Unless expressly stated to the contrary, it is preferred to separate the desired product of the above process steps before proceeding with the next step in the process. Any suitable separation procedure can be used to effect separation such as, for example, where appropriate, extraction, filtration, evaporation, distillation, chroma- tography, etc. Illustrations of suitable separation pro ⁇ cedures can be found in the appropriate example given hereinbelow.
  • the reactions described above are conducted as liquid-phase reactions and hence pressure is generally not significant except as it affects temperature (boiling point) where reactions are conducted at reflux. Therefore, these reactions are generally conducted at pressures of from 300 to 3000 mm mercury and conveniently are conducted at about atmospheric or ambient pressure.
  • the compounds of the present invention exhibit fungicidal activity and especially preventative activity against plant fungal diseases.
  • the compounds are especially effective against powdery mildew fungal diseases caused by organisms such as Erysiphe polyqoni and also against celery late blight producing organisms such as Septoria apii.
  • certain of the present com ⁇ pounds are highly effective against rust causing organisms such as Uromyces phaseoli tipica.
  • the compounds of the invention can be applied in fungicidally effective amounts to fungi and/or their habi- tats, such as vegetative hosts and non-vegetative hosts, e.g., animal products.
  • the amount used will, of course, depend on several factors such as the host, the type of fungus and the particular compound of the invention.
  • the compounds of the invention are usually not applied as pure compunds, but are generally incorporated with carriers to facilitate dispersion of the active fungicidal compounds. Generally, the carriers are biologically inert.
  • the fungicides of the invention can be formulated and applied as granules, powdery dusts, wettable powders, emulsifiable concentrates, solutions, or as any of several other known types of formulations, depending on the desired mode of application.
  • Wettable powders are finely divided particles which disperse readily in water or other dispersant. These compositions normally contain from about 5% to 80% fungicide, and the rest carriers, dispersing agents, emulsifying agents and/or wetting agents. The powder may be applied to the soil as a dry dust, or as a suspension in water. Typical carriers include fuller's earth, kaolin clays, silicas and other highly absorbent, readily wett ⁇ able, inorganic diluents.
  • Typical wetting, dispersing or emulsifying agents include, for example, aryl and alkyl- aryl sulfonates and their sodium salts; alkylamide sulfonates, including fatty methyl taurides; alkylaryl polyether alcohols, sulfated higher alcohols, and polyvinyl alcohols; polyethylene oxides, sulfonated animal and vegetable oils; sulfonated petroleum oils, fatty acid esters of polyhydric alcohols and the ethylene oxide addi ⁇ tion products of such esters; and the addition products of long-chain mercaptans and ethylene oxide.
  • alkylamide sulfonates including fatty methyl taurides
  • alkylaryl polyether alcohols sulfated higher alcohols, and polyvinyl alcohols
  • polyethylene oxides sulfonated animal and vegetable oils
  • sulfonated petroleum oils fatty acid esters of polyhydric alcohols and the ethylene oxide addi ⁇ tion products of
  • the surface-active agent when used, normally comprises from 1% to 15% by weight of the fungicidal composition.
  • Dusts are freely flowing admixtures of the active fungicide with finely divided solids such as talc, natural clays, kieselguhr, pyrophyllite, chalk, diatoma- ceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant.
  • finely divided solids have an average particle size of less than about 50 microns.
  • a typical dust formulation useful herein contains 75% silica and 25% of the toxicant.
  • Useful liquid concentrates include the emulsifi ⁇ able concentrates, which are homogeneous liquid or paste compositions which are readily dispersed in water or other dispersant, and can consist entirely of the fungicide with a liquid or solid emulsifying agent, or can also contain a liqid carrier such as xylene, heavy aromatic naphthas, isophorone, and other nonvolatile organic solvents.
  • these concentrates are dispersed in water or other liquid carrier, and are normally applied as a spray to the area to be treated.
  • fungicidal appli ⁇ cations include simple solutions of the active fungicide in a dispersant in which it is completely soluble at the desired concentration, such as acetone, alkylated naph- thalenes, xylene, or other orqanic solvents.
  • Granular formulations wherein the fungicide is carried in rela ⁇ tively course particles, are of particular utility for aerial distribution or for penetration of cover-crop canopy.
  • Pressurized sprays typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low-boiling dispersant solvent carrier, such as the Freons, can also be used. All of those techniques for formulating and applying fun ⁇ gicides are well known in the art.
  • the percentages by weight of the fungicide can vary according to the manner in which the composition is to be applied and the particular type of formulation, but in general comprise 0.05% to 95% of the toxicant by weight of the fungicidal composition, typically depending on whether the composition is intended for direct application or dilution prior to application.
  • the compounds are typically applied at rates in the range of about from 0.1 to 5 kg/hectare, preferably 0.2 to 3 kg/hectare.
  • the fungicidal compositions can be formulated and applied with other active ingredients, including other fungicides, insecticides, nematocides, bactericides, plant growth regulators, fertilizers, etc.
  • active ingredients including other fungicides, insecticides, nematocides, bactericides, plant growth regulators, fertilizers, etc.
  • equivalent refers to a reagent equal in moles, to the moles of the preceding or succeeding reac- tant recited in that example in terms of finite moles or finite weight or volume.
  • E- and Z-isomers are generated where appropriate and are not separated.
  • geometric isomer and racemic mixtures are used as starting materials and correspondingly isomer mixtures are obtained as products.
  • Example 1 1-(2,4-Dichlorophenoxy)-3,3-dimethylbutan-2-one
  • 8.4 g (0.155 mol) of sodium methoxide was added to a solution containing 24.5 g (0.15 mol) of 2,4-dichlorophenol in 150 ml of methanol at room temperature.
  • the mixture was stirred for 10 minutes 5 and then a solution containing 26.7 g (0.15 mol) of alpha- bromopinacolone was added dropwise.
  • the resulting mixture was heated under reflux for 6 hours, then stirred over ⁇ night (about 15 hours) at room temperature and then fil ⁇ tered.
  • Example 4 Similarly, by following the procedures set forth 5 in Examples 1-3 but using the appropriately substituted phenol and ketone starting materials the following illus ⁇ trative compounds can be prepared.
  • the title compound can be prepared by reacting 0.06 mole of methyl sulfate with 0.1 mole of 3-[2-(2,4- dichlorophenoxy)-3-hydroxy-4,4-dimethylpent-1- enyl] yridine in 200 ml tetrahydrofuran at room tempera- 10 ture.
  • the title compound can then be recovered from the reaction product mixture by appropriate laboratory proce ⁇ dures such as, for example, described in the preceding examples set forth herein.
  • methoxy ethers of the products ⁇ 5 listed in Example 4 hereinabove can be prepared by following the same procedures, including, for example: 3-[2-(2,6-dichlorophenoxy)-3-methoxy-4,4-dimethyl- pent-1-enyl]pyridine;
  • Examples 3 and 4 can be prepared by following the same procedure but replacing 0.06 mole of methyl sulfate with 0.12 mole of allyl chloride and using the appropriate 3- hydroxy starting material.
  • allyl ethers include: 0 3-[2-(2,4-dichlorophenoxy)-3-allylox ⁇ -4,4-dimethyl- pent-1-enyl]pyridine; 3-[2-(2,4-dimethylphenoxy)-3-allyloxy-4,4-dimethyl- pent-1-enyl]pyridine;
  • Such ethers include: 3-[2-(2,4-dichlorophenoxy)-3-(3-chloroallyloxy)-4,4- dimethylpent-1-enyl]pyridine;
  • the title compound can be prepared by reacting a mixture containing 0.11 mole of acetyl chloride; 0.1 mole Q of 3-[2-(2,4-dichlorophenoxy)-3-hydroxy-4,4-dimethylpent-
  • Example 4 can be prepared by following the same procedure, including, for example:
  • Example 7 the compounds of Formula I listed in Table I and the intermediate of Formula A listed in Table II were prepared by following the procedures of Examples 1-3 but using the appropriately substituted phenol and ketone as starting materials. Also for com ⁇ parison purposes the compounds listed in Table III were prepared from the corresponding compound of Formula I via reduction of the alkene double bond via treatment with zinc dust in acetic acid.
  • Example 8 In this example, the compounds of Example 7,
  • Tables I, II and III were tested for effectiveness against a number of different fungi organisms. The parti ⁇ cular organisms and test procedures used are described below. In these tests the compounds were compared against check plants which were also sprayed with the test vehicle
  • Tomato Late Blight The compounds of the invention were tested for the preventative control of the Tomato Late Blight organism Phytophthora infestans. Five- to six-week-old
  • the celery plants were sprayed with 250-ppm solutions of the candidate toxicant mixed with acetone, water and a nonionic emulsifier.
  • the plants were then inoculated with the organism and placed in an environmental chamber and incubated at 66° to 68°F in 100% relative humidity for an extended period of time (approximately 48 hours). Following the incubation, the plants were allowed to dry and then were maintained in a greenhouse for approximately 14 days. Two replicates (i.e., plants) were used for each compound and the check.
  • the percent disease control provided by a given candidate toxicant is based on the percent disease reduction rela ⁇ tive to untreated check plants.
  • Tomato Early Blight Compounds of the invention were tested for the control of the Tomato Early Blight organism Alternaria solani conidia.
  • Tomato (variety Bonny Best) seedlings of 6 to 7 weeks old were used.
  • the tomato plants were sprayed with a 250-ppm solution of the test compound in an acetone-and-water solution containing a small amount of a nonionic emulsifier.
  • the sprayed plants were inoculated one day later with the organism, placed in an environmen ⁇ tal chamber and incubated at 66° to 68°F and 100% relative humidity for 24 hours. Following the incubation, the plants were maintained in a greenhouse for about 12 days. Percent disease control was based on the percent disease development on untreated check plants. Two replicates (plants) were used for each compound and the check. The compounds tested and the averaged results are tabulated in Table IV.
  • Grape Downy Mildew The compounds of the invention were tested for the control of the Grape Downy Mildew organism Plasmopara viticola. Seven-week old Vitis vinifera cultivar Emperor grape seedlings approximately 3 inches tall were used as hosts. The plants were sprayed with a 250-ppm solution of the test compound in acetone and water containing a small amount of nonionic emulsifier. The plants were dried, inoculated with a spore suspension of the organism, placed in a humid environmental chamber and incubated at 66° to 68°F and about 100% relative humidity. After incubation for 2 days, the plants were placed in standing water in a greenhouse at 66-68°F for four days and then placed in an environmental chamber for 48 hours at 100% relative humidity. The plants are then removed from the chamber, dried and then evaluated for the amount of disease con ⁇ trol. The percent disease control provided by a given test compound was based on the percent disease reduction relative to untreated check plants.
  • Bean Rust test was made using pinto bean plants and was conducted as an eradicant test.
  • the pathogen was Uromyces phaseoli tipica.
  • the plants were inoculated with the pathogen and then incubated in an environmental chamber for approximately 24 hours at 100% relative humidity and a temperature of 68° to 70°F.
  • the plants were then removed from the chamber, allowed to dry.
  • the pinto bean plants were then sprayed with a
  • test compound 250-ppm solution of the test compound in an acetone-water mixture containing a small amount nonionic emulsifier.
  • the plants were dried and then maintained in a greenhouse at a 40 to 80% relative humidity and 66° to 72°F for 7 days. The plants were then evaluated for the percent disease control.
  • the percent disease control provided by a given test compound was based on the percent disease reduction relative to untreated check plants.
  • Rice Blast Compounds of this invention were tested for control of the Rice Blast organism Piricularia oryzae, using 10- to 14-day old rice plant seedlings (Calrose M-9 variety). Seedling plants were sprayed with a 625-ppm solution of the test compound in acetone, water and a nonionic emulsifier. The sprayed plants were inoculated 1 day later with the organism in an environmental chamber. After inoculation, the plants were kept in an environmental chamber for about 48 hours under conditions of about 72° to 75°F and about 100% relative humidity. Following the incubation period, the plants were placed in a greenhouse with a temperature of about 72°F and maintained with bottom watering for about 12 to 16 days. The percent disease control provided by a given test compound is based on a comparison of the percentage disease relative to the percent disease development on the untreated check plants.
  • All of the compounds of the present invention further exhibited very substantially superior activity against Celery Late Blight pathogen as compared with comparison compound C-1. More ⁇ over, the closest compound of the present invention (i.e. compound No. 1) to compound C-1 exhibited 100% prevention of Bean Rust pathogen whereas compound C-1 exhibited zero control.
  • Example 9 In this example compound No. 1 (Ar is 2,4-di- chlorophenyl, R is t-butyl and R is hydrogen) and its ketone precursor, compound No. 6, were tested for low dosage preventative fungicidal action with respect to Tomato Early Blight, Celery Late Blight and Bean Powdery Mildew. These tests were conducted in the same manner as described in Example 8 with the exception of the amount of the dosage. The compounds were tested side-by-side in the case of Celery Late Blight and Bean Powdery Mildew. In the case of Tomato Early Blight, the result given for Compound No. 1 is an average of three separate tests. The side-by-side test result for Compound No. 1 with Compound No. 6 is given parenthetically following the averaged result. The dosages used and the results of these tests are summarized in Table V hereinbelow.
  • *ED 50/90 are calculated values of the dosage rate (ppm) needed to obtain 50% control and 90% control. The lower ED 50/90 value, the better the activity.
  • compound No. 1 has superior preventative activity over compound No. 6 with respect to Tomato Late Blight, Celery Late Blight and Bean Powdery Mildew and has particularly good preventative activity with respect to Bean Powdery Mildew.

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

On décrit une 3- AD2-aryloxy-3-hydroxy-3-phenyl ou 3-t-butyl-prop-1-enyl BD pyridine et ses dérivés. Ces composés sont utiles en tant que fongicides, notamment des fongicides agricoles.
PCT/US1985/000433 1985-03-18 1985-03-18 Derives de phenoxyalcenylpyridine, compositions fongicides les contenant, procedes fongicides les utilisant et procedes de preparation de ces derives WO1986005358A1 (fr)

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Application Number Priority Date Filing Date Title
EP19850901761 EP0215778A1 (fr) 1985-03-18 1985-03-18 Derives de phenoxyalcenylpyridine, compositions fongicides les contenant, procedes fongicides les utilisant et procedes de preparation de ces derives
PCT/US1985/000433 WO1986005358A1 (fr) 1985-03-18 1985-03-18 Derives de phenoxyalcenylpyridine, compositions fongicides les contenant, procedes fongicides les utilisant et procedes de preparation de ces derives

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PCT/US1985/000433 WO1986005358A1 (fr) 1985-03-18 1985-03-18 Derives de phenoxyalcenylpyridine, compositions fongicides les contenant, procedes fongicides les utilisant et procedes de preparation de ces derives

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4262000A (en) * 1979-03-09 1981-04-14 Bayer Aktiengesellschaft Combating fungi with 3-substituted pyridine derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4262000A (en) * 1979-03-09 1981-04-14 Bayer Aktiengesellschaft Combating fungi with 3-substituted pyridine derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Reagents for Organic Synthesis published 1975, FIESER and FIESER, Vol. 5 pages 45, 89, 131, 252, 600, 607 and 608 *

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